Diethyl Ether → 2'-Azido-2'-deoxy-5-iodouridine

HRID 634885Notes

Reaction equation

[N:1]([C@@H:4]1[C@H:8]([OH:9])[C@@H:7]([CH2:10][OH:11])[O:6][C@H:5]1[N:12]1[CH:19]=[CH:18][C:16](=[O:17])[NH:15][C:13]1=[O:14])=[N+:2]=[N-:3].[I:20]Cl.CCOCC>CO>[I:20][C:18]1[C:16](=[O:17])[NH:15][C:13](=[O:14])[N:12]([CH:19]=1)[C@@H:5]1[O:6][C@H:7]([CH2:10][OH:11])[C@@H:8]([OH:9])[C@H:4]1[N:1]=[N+:2]=[N-:3]

Participants

Conditions

Temperature: 50 °C

Procedure

To a solution of 2′-azido,2′-deoxyuridine (2.5 g, 9.3 mmoles) in methanol (20 ml) is added ICl (3.3 g, 20.5 mmoles, 2.2 eq.). The mixture is heated at 50° C. for 30 min. After cooling to room temperature, an equal volume of ether is added and the white precipitate is filtered off. The precipitate is stirred in methanolic ammonia (20 ml) at room temperature for 15 min, and then evaporated to dryness to yield 2.81 g (76%) of 5-iodo,2′-azido,2′-deoxyuridine. 1H NMR (300 MHz, methanol -d4) δ 8.58 (s, 1H, H6), 5.88 (d, 1H, H1′, JH1′,H2′=3.5 Hz), 4.46 (t, 1H, H3′, J=5.8 Hz), 4.11 (dd, 1H, H2′, JH1′,H2′=3.9 Hz, J H2′,H3′=5.3 Hz), 4.01 (m, 1H, H4′), 3.91 (dd, 1H, H5′λJgem=12.3 Hz, JH5′,H4′=2.4 Hz) 3.76 (dd, 1H, H5′β, Jgem=12.3 Hz, JH5′,H4′=2.4 Hz). 13C NMR (75 MHz, methanol-d4) δ 163.03, 152.17, 146.50, 88.88, 86.18, 71.21, 67/67, 61.00, 48.15. FAB mass spectrum, (M+H) m/z 396.

Workup

temperatureAfter cooling to room temperature
filtrationthe white precipitate is filtered off
customevaporated to dryness

Sources & evidence

ORD record: ord-3ff9192255cd4e7db979bc59b391cc43
Source dataset: uspto-grants-2001_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06184364B2

Reaction notes

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